Design, Synthesis and Antimicrobial Activities of New Carbon Nanotubes Derivatives

Year 2021, Volume: 11 Issue: 2, 1420 - 1429, 01.06.2021

Aybek Yiğit , Mehmet Hakkı Alma , Yüksel Akınay , Nurettin Mengeş

https://doi.org/10.21597/jist.869281

Abstract

Even though natural products or crops have been more common and popular in the recent, the chemicals without side-effects have been also addressed in various fields of industries due to possibility obtaining the large quantity and more bio-efficacy. In that context, many drugs have been developed for antibacterial activities but the over-uses of those relevant drugs have caused that microorganisms have adapted and evolved resistance against those drugs. Those lead to the researchers to focus on newly synthesized or functionalized molecules. In that context, nanotechnology, especially modified nanocarbon tubes (NCTs), are of the great interest of the various industries. Along with the current study, multi-walled carbon nanotubes (MWCNTs) were functionalized with three steps. Firstly, the carbon nanotube with a carboxylic acid tip on its surface was commercially purchased and then converted into acyl chloride, and later converted into a more reactive group. Then, the nucleophilic amino group such as diethylene triamine is bonded onto the carbon nanotube. Finally, after the carbon nanotube material with amine groups was functionalized with boric acid, carbon nanotube molecules carrying boric acid molecules were synthesized. Following modification and functionalization of MWCNTs, the newly synthesized molecules were characterized using FT-IR, SEM, TEM and XPS. After chemical characterization, the relevant molecules were screened for their anti-bacterial activities in comparison to those of well-known antibiotics. For anti-bacterial assays, molecules were tested against K. pneumoniae, E. coli, P.aeruginosa, S. aureus and B. subtilis. Concerning the findings of the antibacterial assays, concentrations of 40 and 80 μg /mL exhibited a range of activities but in parallel with those of standard antibiotics whereas the lower concentration, viz. 5, 10 and 20 μg / mL did not exhibit any activities. The highest activity was noted for 80 μg / mL, in comparison to those of antibiotics and other concentrations, against B. subtilis, with a 23 mm inhibition zone.

Keywords

Carbon nanotube,, disc diffusion method,, primary amine,, antibacterial activity

Supporting Institution

This study was funded by both Van Yüzüncü Yil University (Project Number: 2019-FDK-7816) and Igdir University (Project number: 2019-FBE-A27). Authors thank to The head of the center of Scientific and Application Center in Van Yüzüncü Yil University for spectral support. Also, bioactivity studies was made in Staff Chemical Reagent Company.

Project Number

Van Yüzüncü Yil University (Project Number: 2019-FDK-7816) and Igdir University (Project number: 2019-FBE-A27)

References

• Al-Jumaili A, Alancherry S, Bazaka K, Jacob M, 2017. Review on the antimicrobial properties of carbon nanostructures. Materials, 10(9): 1066.
• Allahverdiyev AM, Abamor ES, Bagirova, M, & Rafailovich M, 2011. Antimicrobial effects of TiO2 and Ag2O nanoparticles against drug-resistant bacteria and leishmania parasites. Future microbiology, 6(8):933-940.
• Alshehri R, Ilyas AM, Hasan A, Arnaout A, Ahmed F, Memic A, 2016. Carbon nanotubes in biomedical applications: factors, mechanisms, and remedies of toxicity: miniperspective. Journal of medicinal chemistry, 59(18): 8149-8167.
• Amenta V, Aschberger K, 2015. Carbon nanotubes: potential medical applications and safety concerns. Wiley Interdisciplinary Reviews: Nanomedicine and Nanobiotechnology, 7(3): 371-386.
• Amiri A, Zardini HZ, Shanbedi M, Maghrebi M, Baniadam M, Tolueinia B, 2012. Efficient method for functionalization of carbon nanotubes by lysine and improved antimicrobial activity and water-dispersion. Materials Letters, 72: 153-156.
• Anar M, Orhan F, Alpsoy L, Gulluce M, Aslan A, Agar G, 2016. The antioxidant and antigenotoxic potential of methanol extract of Cladonia foliacea (Huds.) Willd, Toxicology and Industrial Health, 32 (4): 721-729.
• Arumugasamy SK, Govindaraju SK, Yun K, 2020. Electrochemical Sensor for Detecting Dopamine Using Graphene Quantum Dots Incorporated with Multiwall Carbon Nanotubes. Appl. Surf. Sci., 145294.
• Aslan S, Deneufchatel M, Hashmi S, Li N, Pfefferle LD, Elimelech M, Van Tassel PR, 2012. Carbon nanotube-based antimicrobial biomaterials formed via layer-by-layer assembly with polypeptides. Journal of colloid and interface science, 388(1): 268-273.
• Berber İ, 2013. Sinop’da yetişen bazı bitkilerin metanolik ekstraktlarının antibakteriyal ve antifungal aktivitelerinin belirlenmesi. Karaelmas Science and Engineering Journal, 3(1): 10-16.
• Cao Y, Mohamed AM, Mousavi M, Akinay Y, 2020. Poly (pyrrole-co-styrene sulfonate)-encapsulated MWCNT/Fe-Ni alloy/NiFe2O4 nanocomposites for microwave absorption. Materials Chemistry and Physics, 124169.
• Cataldo F, Da Ros T, 2008. Medicinal chemistry and pharmacological potential of fullerenes and carbon nanotubes (Vol. 1). Springer Science & Business Media.
• Chen H, Wang B, Gao D, Guan M, Zheng L, Ouyang H, Feng W, 2013. Broad‐spectrum antibacterial activity of carbon nanotubes to human gut bacteria. Small, 9(16): 2735-2746.
• Chhipa H, 2017. Nanofertilizers and nanopesticides for agriculture. Environmental chemistry letters, 15(1): 15-22.
• Cui L, Huang H, Ding P, Zhu S, Jing W, Gu X, 2020. Cogeneration of H2O2 and OH via a novel Fe3O4/MWCNTs composite cathode in a dual-compartment electro-Fenton membrane reactor. Separation and Purification Technology, 237: 116380.
• De La Torre-Roche R, Hawthorne J, Deng Y, Xing B, Cai W, Newman LA, White JC, 2013. Multiwalled carbon nanotubes and C60 fullerenes differentially impact the accumulation of weathered pesticides in four agricultural plants. Environmental Science & Technology, 47(21): 12539-12547.
• Dizaj SM, Mennati A, Jafari S, Khezri K, Adibkia K, 2015. Antimicrobial activity of carbon-based nanoparticles. Advanced pharmaceutical bulletin, 5(1): 19.
• Eatemadi A, Daraee H, Karimkhanloo H, Kouhi M, Zarghami N, Akbarzadeh A, Joo SW, 2014. Carbon nanotubes: properties, synthesis, purification, and medical applications. Nanoscale research letters, 9(1): 393.
• Hu C, Hu S, 2009. Carbon nanotube-based electrochemical sensors: principles and applications in biomedical systems. Journal of Sensors 2009.
• İlçim A, Dığrak M, Bağcı E, 1998. Bazı bitki ekstraktlarının antimikrobiyal etkilerinin araştırılması. Turkish Journal of Biology, 22: 119-125.
• Kang S, Herzberg M, Rodrigues DF, Elimelech M, 2008. Antibacterial effects of carbon nanotubes: size does matter!. Langmuir, 24(13): 6409-6413.
• Kassem A, Ayoub GM, Malaeb L, 2019. Antibacterial activity of chitosan nano-composites and carbon nanotubes: A review. Science of the total environment, 668: 566-576.
• Kassem A, Ayoub GM, Malaeb L, 2019. Antibacterial activity of chitosan nano- composites and carbon nanotubes: a review. Science of the total environment, 668: 566-576.
• Khabashesku VN., & Pulikkathara MX, 2006. Chemical modification of carbon nanotubes. Mendeleev Communications, 16(2): 61-66.
• Li H, Fedorova OS, Grachev AN, Trumble WR, Bohach GA, Czuchajowski L, 1997. A series of meso-tris (N-methyl-pyridiniumyl)-(4-alkylamidophenyl) porphyrins: Synthesis, interaction with DNA and antibacterial activity. Biochimica et Biophysica Acta (BBA)-Gene Structure and Expression, 1354(3): 252-260.
• Liu S, Ng AK, Xu R, Wei J, Tan CM, Yang Y, Chen Y, 2010. Antibacterial action of dispersed single-walled carbon nanotubes on Escherichia coli and Bacillus subtilis investigated by atomic force microscopy. Nanoscale, 2(12): 2744-2750.
• Ma R, Hu J, Cai Z, Ju H, 2014. Facile synthesis of boronic acid-functionalized magnetic carbon nanotubes for highly specific enrichment of glycopeptides. Nanoscale, 6: 3150-3156.
• Mocan L, Ilie I, Matea C, Tabaran F, Kalman E, Iancu C, Mocan T, 2014. Surface plasmon resonance-induced photoactivation of gold nanoparticles as bactericidal agents against methicillin-resistant Staphylococcus aureus. International journal of nanomedicine, 9: 1453.
• Mondal A, Basu R, Das S, Nandy P, 2011. Beneficial role of carbon nanotubes on mustard plant growth: an agricultural prospect. Journal of Nanoparticle Research, 13(10): 4519.
• Onbaşılı D, Altuner EM, Çelik GY, 2011. Mnium marginatum Özütlerinin antimikrobiyal aktivitesi, Kastamonu Üniversitesi Orman Fakültesi Dergisi, 11 (2): 205-208.
• Sah, U., Sharma, K., Chaudhri, N., Sankar, M., & Gopinath, P. (2018). Antimicrobial photodynamic therapy: Single-walled carbon nanotube (SWCNT)-Porphyrin conjugate for visible light mediated inactivation of Staphylococcus aureus. Colloids and Surfaces B: Biointerfaces, 162, 108-117.
• Salam, M. A., & Burk, R. (2017). Synthesis and characterization of multi-walled carbon nanotubes modified with octadecylamine and polyethylene glycol. Arabian Journal of Chemistry, 10, S921-S927.
• Seo Y, Hwang J, Kim J, Jeong Y, Hwang MP, Choi J, 2014. Antibacterial activity and cytotoxicity of multi-walled carbon nanotubes decorated with silver nanoparticles. International Journal of Nanomedicine, 9: 4621.
• Sokolov VI, Stankevich IV, 1993. The fullerenes—new allotropic forms of carbon: molecular and electronic structure, and chemical properties. Russian Chemical Reviews, 62(5): 419.
• Vecitis CD, Zodrow KR, Kang S, Elimelech M, 2010. Electronic-structure-dependent bacterial cytotoxicity of single-walled carbon nanotubes. ACS nano, 4(9): 5471-5479.
• Wang JT, Chen C, Wang E, Kawazoe Y, 2014. A new carbon allotrope with six-fold helical chains in all-sp 2 bonding networks. Scientific reports, 4: 4339.
• Zardini HZ, Amiri A, Shanbedi M, Maghrebi M, Baniadam M, 2012. Enhanced antibacterial activity of amino acids-functionalized multi walled carbon nanotubes by a simple method. Colloids and Surfaces B: Biointerfaces, 92: 196-202.